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Combs' Defense Cross-examines Cassie Ventura; Ventura Testified Combs Abused Her and Orchestrated Sex Performances. Aired 2-2:30p ET

Aired May 15, 2025 - 14:00   ET

THIS IS A RUSH TRANSCRIPT. THIS COPY MAY NOT BE IN ITS FINAL FORM AND MAY BE UPDATED.

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[14:00:29]

BRIANNA KEILAR, CNN CO-ANCHOR OF "CNN NEWS CENTRAL": Happening now, we are following breaking new details and Sean "Diddy" Combs' racketeering and sex trafficking trial in New York. His ex-girlfriend, Cassie Ventura, is on the stand right now. She's been facing cross- examination for just about three hours. Questions so far today have mostly centered around text messages, some detailing their sexual encounters that she and Combs, these text messages sent one another during their 11-year relationship.

The defense is trying to convince jurors that Ventura was not coerced into acts by Combs, but rather she was consenting.

BORIS SANCHEZ, CNN CO-ANCHOR OF "CNN NEWS CENTRAL": Just a short time ago, the judge told the defense that it has until tomorrow afternoon to wrap up their cross-examination. Prosecutors yesterday, said it was possible that Ventura who is well into her third trimester of pregnancy, could go into labor this weekend. With us now are Dave Aronberg, a former State Attorney for Palm Beach County in Florida; and Attorney and Legal Affairs Commentator, Areva Martin. Also with us, Richard Gabriel, a Veteran Trial Consultant and President of Decision Analysis. He's actually the author of "Acquittal," which highlights his work on several high-profile cases. Also with us is Jem Aswad, Executive Music Editor for Variety. Thank you all for being with us.

I want to get to some of the latest details that we've gotten from the courtroom, specifically some of the text messages that have been exchanged between Cassie Ventura and Combs, and specifically the defense asking Cassie Ventura about a conversation in March, 2017 when Ventura told Combs to, essentially, stop playing the victim, saying that she loves freak offs when we both want them. And then, she was asked about that text message. She said, I would say that loving freak offs were just words at that point.

Dave, I wonder what you make of the defense going through these text messages, trying to paint a picture of cohesiveness and even agreement over these sexual encounters that the prosecution is saying were coerced.

DAVE ARONBERG, FORMER STATE ATTORNEY, PALM BEACH COUNTY, FLORIDA: I definitely think the defense has won some points because although the prosecution tried to take the sting out of some of this by showing that she may have texted Diddy that she liked freak offs, but at some point, this was force, fraud or coercion, that it was against her will and she was just trying to please a man she loved, unrequited love. But still, jurors are human beings. And when they see this, they're going to cast some doubts, I think, have some doubts in their minds over whether this was consensual.

Now, the prosecution gets a chance to rehabilitate the witness later, and that's when Cassie can say, I said what I said, but you can see by my actions, by his actions that this wasn't consensual. I mean, he beat me up. He forced me to do things against my will, even if I was into it at the beginning just to please him, it doesn't mean that I consented the whole way through. But jurors are going to come at this from their own life experiences with freak offs are something foreign, unique, weird. And if they think that Cassie, at some point, was part of it willingly, yeah, that's going to be really bad for the prosecution.

KEILAR: Richard, when she says that I love our freak offs, when we both want it. I mean, when we both want it, inherent in that is that sometimes she didn't. And I wonder what the jury might think about that.

RICHARD GABRIEL, TRIAL CONSULTANT: Well, I think what the defense is really trying to do right now, is to establish Cassie as has her own agency. In other words, all of this really leads up to them establishing she is independent. She's making her own decisions. She's communicating with Sean about the relationship. She's talking in a very independent way. So, they're trying to not just establish that sometimes she actually participated willingly in this, i.e., consensual -- consensually, but also that she is her own person. In other words, she could have walked away at various points and not have participated.

Jurors are going to be fundamentally confronted with these two different versions, these two different character portrayals of who Cassie Ventura is and ultimately, decide what it is. The complication of the relationship is a key point for the defense.

SANCHEZ: Imran, notably, there was one message, and I believe we have the graphic to show it, in which Cassie Ventura is describing to Combs, going back and forth in her mind with wanting and not wanting to do it, these stage sexual encounters. She said the last time was a mistake and since has made me feel a little dirty and grimy as opposed to sexual and spontaneous.

[14:05:00]

It seems like jurors could see this as her perhaps initially, wanting to do something with him, and eventually, finding out that it was not what she signed up for, right?

IMRAN ANSARI, FORMER PROSECUTOR & CRIMINAL DEFENSE ATTORNEY: Right, absolutely. So, you're going to have to juxtapose the testimony from the prosecution on direct with what we are seeing now on cross. And if there's any question in terms of raising that reasonable doubt, whether there were some consensual times or this was just regret rather than being coerced into something that she did not want to do at the time, that's going to be something that the defense is going to want to hit home to that jury.

So, you see the building blocks with this cross-examination, in trying to raise that reasonable doubt, taking the narrative that the prosecution was able to get out from her on direct and raising those questions in the jury's mind, ultimately, saying that she was a willing participant and if anything, there may have been some regret after the fact, but it wasn't that she was coerced or forced into any of these acts. And I think that's what the defense is trying to do here. Take it apart, the direct examination piece by piece and we'll see that going forward.

KEILAR: And Jim, I wonder, as the defense had asked Ventura, they were talking to her about her 21st birthday in 2007, which Combs attended. They noted that she was a celebrity in her own right by then. But, can you talk a little bit about that? And also, the fact that she had this 10-year record deal with Bad Boy, which was Sean Combs' label, but at that point, she'd done one album and after this event, she'd never do another one. How unusual is that?

JEM ASWAD, EXECUTIVE MUSIC EDITOR, VARIETY: I mean, all of -- she was a mid-level star at that time. I was working at MTV News at the time. We covered her quite a bit. She had previously worked with a producer songwriter named Ryan Leslie, who's the person basically credited with discovering her. Diddy kind of pushed him out of the picture, made one record, a 10-year deal. I'm not sure if it was 10 years or 10 albums, is a very, very restrictive deal. I mean, that locks you up for your career and then some.

So, that says something about the kind of deals that not only him, but like most record labels were signing at the time. It was usually seven albums, 10 is a lot. But she was established, but he controlled her career. I mean, there -- these contracts lock you up so you can't do anything else. There's a singer right now named Sky Ferreira, who rightly or wrongly says she's been prevented from releasing music because of the contract she was under. It happens all the time.

So, he had a very strong hand in not only her career, but obviously her personal life. And I just wonder, like, I don't think there are probably any texts saying, I love it when you drag me down the hall and beat me when I'm trying to escape. Sorry, I just had to say that.

KEILAR: Yeah, no, it was 10 albums to your point, not 10 years.

SANCHEZ: Yeah, yeah, yeah. I did want to ask you, Jim, to follow that up because, to the question of coercion, to the question of the power dynamic in their relationship, she was 19 years old when they met, and if you do the math, that was roughly 2009, I believe. That means that by the time that she was a young child, Sean Combs was already a superstar, known around the world, touring, one of the biggest selling artists of the '90s. So, she undoubtedly, probably looked up to him, aspiring to be a singer, aspiring to be in the music industry. So, that also speaks to that power dynamic. Could you give us some context of who Sean Combs was as she was becoming a young woman and why she might have felt so attracted to him?

ASWAD: You know, someone like him swoops in and says, I'm going to make you a star. And she hits, I think she's on the record as saying that things didn't turn dark until later. That's a very, very common syndrome. Now, his temper and his penchant for some violence is a matter of public record. Less so with women at the time, but like, there was a -- there was an executive that he either beat or had his thugs beat up with a champagne bottle that was settled out of -- afraid of him. He was extremely powerful, extremely wealthy, and his temper like definitely, kept people behaving a certain way around him.

He was one of the most powerful people in the music business for 20 some years because he was so wealthy and because he had so many people who were willing not only to do what he wanted, but were very afraid to speak out against him.

[14:10:00]

Now, I've been in the industry ever since he first started coming around, basically. And you heard about his temper. You heard that people were afraid of him. The violent was -- violence was a matter of public record. I did not hear about freak offs. I did not hear about a lot of these things that are coming to light now. And neither did a lot of the people that I know.

KEILAR: Yeah, that is really interesting, Jim. Areva, we knew that there was a settlement, right? When Cassie Ventura filed her lawsuit, very quickly, Combs settled. We only learned the amount of the settlement when Ventura re revealed, she'd received $20 million, which is a lot of money, that's going to folks on this jury, maybe it's not as much money to someone like Sean Combs. It is a lot of money objectively to people on this jury. How is the defense going to use that?

AREVA MARTIN, ATTORNEY & LEGAL AFFAIRS COMMENTATOR: Well, a part of what the defense is saying is that she stuck around for the money, and that she enjoyed the perks and benefits of being his girlfriend and being in a relationship with him, and that she has profited from this story that she's telling to the jury. But, I don't -- I think jurors are smart enough to appreciate the difference in a civil lawsuit. And some people will feel like the violence that she was subjected to the $20 million was not nearly enough.

There are people who are shocked at how little $20 million is when you think about the amount of wealth that he has and the violence that she endured in this relationship. And this whole notion, Brianna, of consent, I think separate that from the violence. If this were a case where you had the text messages and the love -- comments that she's making in these text messages, and you didn't have the threats of blackmail, and you didn't have the actual physical violence that the jury now knows about, then I think perhaps this notion of consent makes more sense.

But when you pair the violence with the comments, I don't think it's going to be lost on this jury that yes, at some point, the early stages of this relationship, maybe the honeymoon stages, she may have been willing to participate in these freak offs to satisfy him because she loved him. But later on, as the relationship goes on, it's very clear that something changes and the level of violence and the level of threats clearly indicate force, clearly indicate coercion. So, the jurors are going to have to grapple with what do you do with this violence that they've heard about and seen with the very eyes in these videos.

KEILAR: Everyone, stay with us. Great points that you're raising here. We're going to have more just ahead on "CNN News Central." Our coverage of the criminal trial of Sean "Diddy" Combs will continue as the defense team is still cross-examining his former girlfriend and key witness for the prosecution, Cassie Ventura, painting a very different picture of their relationship. We'll have that ahead.

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[14:17:44]

SANCHEZ: We are continuing to follow the latest developments in the Sean "Diddy" Combs federal sex trafficking trial. His ex-girlfriend, Cassie Ventura, now being cross-examined by the defense in her third day of testimony. She's testified now for more than 12 hours.

KEILAR: And earlier, the defense called Ventura, "the most important witness." And moments ago, Combs' attorney questioned her about texts that she sent to Combs in 2013 where she expressed jealousy over his relationship with one of his exes. Ventura confirming it made her really upset. We have Dave Aronberg, Imran Ansari, Richard Gabriel, Jem Aswad, and Areva Martin with us.

Areva, what does that go to establishing her jealousy?

MARTIN: Well, a big part of the defense's case, Brianna, is that Cassie Ventura was jealous and that they often got into fights, physical fights, and we'll hear, I'm sure from the defense, times, they'll ask her about times where she may have initiated fights with Sean Combs. They're trying to establish that this was not just Combs initiating violence, but that she too initiated violence because she was jealous over relationships he had with other women.

Again, all of this is a part of the defense's strategy to show that this was a woman who knew what she was doing, knew she was in a relationship with a man that had other girlfriends, had other women, that she participated willingly in these sexual acts with outside people, and that she had an opportunity to leave the relationship if she thought that it was something she no longer wanted to participate in.

But I keep going back to the way that the concept or the word 'coercion' is interpreted by courts. When you look at the sex trafficking statute, that's so important to this case, and that definition of coercion is interpreted broadly by courts to include physical threats, to include psychological manipulation, withholding of basic necessities. And we've heard a lot about all of those elements in Cassie's direct examination. I think it will be revisited in the cross, the rehabilitation or the redirect from the prosecution that's likely to happen tomorrow.

SANCHEZ: And Richard, I wonder when it comes to specifically the statutes that the prosecution is alleging that Combs violated, whether some of this questioning about their relationship, previously, her consent in it, what that means for the actual laws that the prosecution is claiming that were broken here and whether the defense is chipping away at the threshold of Combs actually having committed not only sex trafficking, but racketeering as well?

[14:20:28]

GABRIEL: Well, you have to understand that both direct and cross- examination are setting up arguments for both sides for two reasons. One, when they get to the experts, each side is going to have their own experts to say, psychologically, this does meet the threshold for coercion and sort of her being under the thumb of Sean Combs. Obviously, the defense saying -- the defense's experts saying, this doesn't meet how you see all (ph) of her independence and her ability to leave.

And then secondarily, it's going to be tied to what they're going to be arguing, what the actual statutes mean, what the legal definitions are, and as a result, jurors, but fundamentally have to get their own gut feeling as to whether there's real participation on her part. And this goes to a lot to the jury selection process and how they see Cassie Ventura, how they see the role of victims in these kinds of cases. We have seen a sea change in recently, in terms of people being aware of how coercive and abusive relationships do work, how people can be groomed by being first thought of very highly and laden with lots of gifts. And then later on, the thumb comes down and then the coercion and the threats start.

So, I think jurors are much more aware of that, whether that fits the model that they see, or whether they think no, she actually is exhibiting some real independence here, that's up for the personal interpretation of the jurors.

KEILAR: Dave, I wonder what you think of this particular part where, as the defense attorney, these text exchanges with Cassie Ventura, she says this isn't about what I feel is relevant right now, right? Because there's a lot over (ph). One, I imagine we'll see some of what may or have been skipped over on redirect when her attorneys are -- or when the prosecution is questioning her. But also, what's the effect on the jury basically being told by Cassie Ventura, you're not getting the whole story.

ARONBERG: Yeah, juries always want to know what they're missing. They don't want lawyers to play games with them. And so, if Cassie is saying you're not reading the whole message, that does play into the juror's natural suspicions. Then, the prosecutor will get up on redirect and hopefully then, put everything into context. See, you're trying to convince the jury that relationships are complicated. This isn't Hollywood. This is the real world.

And in a complicated relationship, you could have one side being in love with the other and the other side abusing that person. It could happen, and you could have a woman still be in love with someone who's an abuser. We saw this in the Harvey Weinstein case. That was the whole prosecution theory, that sometimes you have people who are victims of sexual assault remain friends with that person. You have to just get the jury to understand it, that life is a lot more complicated, a lot more nuanced. When some jurors may just say it's all or nothing.

SANCHEZ: I do wonder, Imran, how you see the jury reacting to all of this because even just an observer who's sort of documenting, it is overwhelming not only the contours of their relationship, the power dynamic, the things that she endured, the sexually explicit images, et cetera, et cetera, but the star power of it. You're in court with these two celebrities and for example, Sean "Diddy" Combs, earlier in the trial, earlier in the week, he had his twin daughters there. They're not going to be there now because they're headed off to prom. He's making heart symbols at one of the partners of one of his attorneys. I just wonder how they receive all of that, because it is undoubtedly overwhelming.

ANSARI: Yeah, it's a lot. And that's why the jury selection process, in this particular case, would've been very nuanced. You would want jurors who are going to be on that jury, who aren't going to be starstruck, who aren't going to be distracted from the star power, from the different stories and testimony coming in about people who are in the entertainment industry, and that would somehow distract them from what is happening in court, which is most important, which is the receipt of the evidence, receipt of the testimony, and then ultimately, taking that evidence and putting it and juxtaposing it to the law that the judge is going to instruct them on.

So during the jury selection process, I believe both sides would've tried to parse out those who may have been wanting to be on this jury for the wrong reasons.

[14:25:00]

And the jurors now, getting all this evidence, it's evidence that is weighty. There's the video of Cassie Ventura. It's hard to watch. And in the background of all of this is the star power of Diddy Combs sitting there and now on trial. But you want that jury focused on the evidence, you want them to be considering what is being told to them in testimony and the exhibits. And ultimately, when they receive the case to deliberate, they're putting away that star power and concentrating on that evidence and how the law has been instructed to them by the judge.

SANCHEZ: Everyone, please stand by. We have to sneak in a quick break. We have much more of our coverage ahead as Sean "Diddy" Combs' ex- girlfriend, Cassie Ventura, faces questions from his defense team. Don't go anywhere.

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